西托癸内酯B和C的首次不对称全合成及绝对构型测定

The first asymmetric total syntheses and determination of absolute configurations of xestodecalactones B and C.

作者信息

Liang Qiren, Zhang Jiyong, Quan Weiguo, Sun Yongquan, She Xuegong, Pan Xinfu

机构信息

Department of Chemistry, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P.R. China.

出版信息

J Org Chem. 2007 Mar 30;72(7):2694-7. doi: 10.1021/jo070159v. Epub 2007 Mar 9.

DOI:10.1021/jo070159v

PMID:17346089

Abstract

The first efficient asymmetric total syntheses of xestodecalactones B and C have been accomplished in 10 steps with an overall yield of 22 and 20.2%, respectively. The key steps involve the utility of Evans oxazolidinone-mediated syn-aldol condensations to establish the C-9 configuration and the macrolide ring formation by intramolecular acylation. The absolute configurations of xestodecalactones B and C have been determined via these syntheses.

摘要

西托内酯B和C的首次高效不对称全合成已通过10步反应完成，总产率分别为22%和20.2%。关键步骤包括利用埃文斯恶唑烷酮介导的顺式羟醛缩合反应来构建C-9构型，以及通过分子内酰化反应形成大环内酯环。通过这些合成确定了西托内酯B和C的绝对构型。